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EP1781648A2 - 1,3,4-oxadiazol-2-ones as ppar delta modulators - Google Patents

1,3,4-oxadiazol-2-ones as ppar delta modulators

Info

Publication number
EP1781648A2
EP1781648A2 EP05767047A EP05767047A EP1781648A2 EP 1781648 A2 EP1781648 A2 EP 1781648A2 EP 05767047 A EP05767047 A EP 05767047A EP 05767047 A EP05767047 A EP 05767047A EP 1781648 A2 EP1781648 A2 EP 1781648A2
Authority
EP
European Patent Office
Prior art keywords
phenyl
alkyl
disease
compound
aryl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP05767047A
Other languages
German (de)
English (en)
French (fr)
Inventor
Daniel G. Mcgarry
Jochen Goerlitzer
Stefanie Keil
Karen Chandross
Jean Merrill
Wolfgang Wendler
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Aventis Pharmaceuticals Inc
Original Assignee
Aventis Pharmaceuticals Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Aventis Pharmaceuticals Inc filed Critical Aventis Pharmaceuticals Inc
Publication of EP1781648A2 publication Critical patent/EP1781648A2/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/12—Ophthalmic agents for cataracts
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/24—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Definitions

  • PPARdelta also known as PPARbeta
  • PPARdelta is expressed in a broad range of mammalian tissue, but little information regarding its biological functions or the full array of genes regulated by the receptor have been elucidated. However, it has recently been found that agonists may be useful to treat conditions such as dyslipedemia and certain dermatological conditions, while antagonists may be useful to treat osteoporosis or colorectal cancer (D. Sternbach, in Annual Reports in Medicinal Chemistry, Volume 38, A. M. Doherty, ed., Elsevier Academic Press, 2003 pp. 71-80). PPARdelta appears to be significantly expressed in the CNS; however much of its function there still remains undiscovered.
  • Ri is H, halogen, -galkyl, C ⁇ - 6 alkoxy, C ⁇ - 6 pe ⁇ fluoroalk3.1; hydroxy -ealkyl, nitro, cyano, and Ci-ealkylamino; and R 2 is substituted or unsubstituted phenyl, pyridinyl or thienyl wherein the substituents are selected from the group consisting of halogen, C M salkyl, C 2 - 6 alkenyl, Ci-galkoxy, C ⁇ _ 6 perfluoroalkyl, Ci- 6 alkylthio, hydroxy, hydroxyCi - 6 alkyl, Ci- 4 acyloxy, nitro, cyano, C ⁇ - 6 alkylsulfonyl, amino, Ci-ealkylamino and Cn- ⁇ a-lkoxycarbonyl; with the proviso that when Z is -O(CH 2 ) n - or -SO 2 (CH 2 ) n --,
  • C 3 . 8 cycloalkyl means cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.
  • C 3 - 8 cycloalkyld- 6 alkyr means that the C 3 - 8 cycloalkyl as defined herein is further attached to C ⁇ - 6 alkyl as defined herein.
  • stereoisomers is a general term used for all isomers of the individual molecules that differ only in the orientation of their atoms in space. Typically it includes mirror image isomers that are usually formed due to at least one asymmetric center, (enantiomers). Where the compounds according to the invention possess two or more asymmetric centers, they may additionally exist as diastereoisomers, also certain individual molecules may exist as geometric isomers (cis/trans). It is to be understood that all such isomers and mixtures thereof in any proportion are encompassed within the scope of the present invention.
  • Substituted means substituted by 1 to 2 substituents independently selected from the group consisting of C ⁇ - 6 alkyl, d- 6 perfluoroalkyl, hydroxy, -CO 2 H, an ester, an amide, Ci -C 6 alkoxy, Ci -C 6 perfluoroalkoxy,-NH 2 , CI, Br, I, F, -NH-lower alkyl, and -N(lower alkyl) 2 .
  • the compounds and salts of the present invention may exist in several tautomeric forms, including the enol and imine form, and the keto and enamine form and geometric isomers and mixtures thereof. All such tautomeric forms are included within the scope of the present invention.
  • ARYL is phenyl or pyridinyl, wherein said phenyl or pyridinyl is optionally substituted with one or more substituents selected from the group consisting of halogen, d- 6 alkyl, C 2 - 6 alkenyl, d- 6 alkoxy, d- 6 perfluoroalkyl; Ci- 6 alkylthio, hydroxy, hydroxyC ⁇ - 6 alkyl, d- 4 acyloxy, nitro, cyano, d- 6 alkylsulfonyl, amino, C ⁇ - 6 alkylamino and Ci- 6 alkoxycarbonyl; Z is -O(CH 2 ) n -, -SO 2 (CH 2 ) lake-, -(CH 2 ) n -Y-(CH 2 ) n -,-(CH 2 ) n -CO-, -O(CH 2 ) n -CO-, or -(CH 2 ) n
  • Clinical disease typically becomes manifest around day 8-10 after inoculation, observed as a broad spectrum of behavioral anomalies ranging from mild gait disturbances and tail atony to complete paralysis and death. Weight loss typically occurs. In animals that survive, spontaneous recovery occurs, accompanied by variable recovery of most motor function. Depending on the species, allergen, and methodology used, animals tested by the EAE model may experience a single (acute EAE) or several (chronic relapsing EAE) attacks.
  • the drug or treatment of choice may be administered before immunization, during the nonsymptomatic period or during the clinical disease.
  • STAGE:7 DEATH Treatment is begun on day 10 after immunization. Since the disease symptoms in this model typically appear 10-11 days after inoculation, this time point may be considered to represent the initial phase of an acute episode of MS. It is judged that this delay of the start of treatment mimics the clinical situation more closely than the traditionally used protocols where drugs are administered at the time of, or even before, inoculation (Teitelbaum D. et al., Proc Natl Acad Sci USA 1999; 96: 3842-3847 and Brod S. A., et al., Ann Neurol 2000; 47: 127-131).
  • This invention is further illustrated by the following examples of compounds used herein which are provided for illustration purposes and in no way limit the scope of the present invention. Svnthetic Examples

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Diabetes (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Urology & Nephrology (AREA)
  • Endocrinology (AREA)
  • Vascular Medicine (AREA)
  • Hospice & Palliative Care (AREA)
  • Emergency Medicine (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Child & Adolescent Psychology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
EP05767047A 2004-04-01 2005-03-30 1,3,4-oxadiazol-2-ones as ppar delta modulators Withdrawn EP1781648A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US55842004P 2004-04-01 2004-04-01
PCT/US2005/010855 WO2005097763A2 (en) 2004-04-01 2005-03-30 1,3,4-oxadiazol-2-ones as ppar delta

Publications (1)

Publication Number Publication Date
EP1781648A2 true EP1781648A2 (en) 2007-05-09

Family

ID=34972960

Family Applications (1)

Application Number Title Priority Date Filing Date
EP05767047A Withdrawn EP1781648A2 (en) 2004-04-01 2005-03-30 1,3,4-oxadiazol-2-ones as ppar delta modulators

Country Status (15)

Country Link
US (2) US7638539B2 (ru)
EP (1) EP1781648A2 (ru)
JP (1) JP4813461B2 (ru)
CN (1) CN1956984B (ru)
AU (1) AU2005230838A1 (ru)
BR (1) BRPI0508180A (ru)
CA (1) CA2561230A1 (ru)
IL (1) IL178166A0 (ru)
MA (1) MA28563B1 (ru)
NO (1) NO20064951L (ru)
NZ (1) NZ549823A (ru)
RU (1) RU2365589C2 (ru)
SG (1) SG151336A1 (ru)
WO (1) WO2005097763A2 (ru)
ZA (1) ZA200607852B (ru)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BRPI0508180A (pt) * 2004-04-01 2007-08-07 Aventis Pharma Inc 1,3,4-oxadiazol-2-onas como moduladores de ppar delta e seu uso deste
RU2375358C2 (ru) * 2004-04-01 2009-12-10 Авентис Фармасьютикалз, Инк. 1,3,4-оксадиазол-2-оны в качестве модуляторов ppar-дельта и их применение
US8053598B2 (en) 2004-05-05 2011-11-08 High Point Pharmaceuticals, Llc Compounds, their preparation and use
ATE486055T1 (de) 2004-05-05 2010-11-15 High Point Pharmaceuticals Llc Neue verbindungen, ihre herstellung und verwendung
JP5052511B2 (ja) 2005-06-30 2012-10-17 ハイ ポイント ファーマシューティカルズ，エルエルシー Ｐｐａｒデルタ活性化因子としてのフェノキシ酢酸
EP1931337B1 (en) 2005-09-29 2013-10-23 Sanofi Phenyl- and pyridinyl- 1, 2 , 4 - oxadiazolone derivatives, processes for their preparation and their use as pharmaceuticals
CA2631390C (en) 2005-12-22 2014-03-11 Per Sauerberg Phenoxy acetic acids as ppar delta activators
JP2009529512A (ja) 2006-03-09 2009-08-20 ハイ ポイント ファーマシューティカルズ，リミティド ライアビリティ カンパニー 新規な化合物、それらの製造法、及び使用法
JP2013506686A (ja) 2009-09-30 2013-02-28 プレジデント アンド フェロウズ オブ ハーバード カレッジ オートファジー阻害遺伝子産物の変調によりオートファジーを変調する方法
BRPI1107312B1 (pt) * 2011-11-25 2021-09-08 Universidade Federal De Santa Catarina Composto de acil-hidrazona
EP3043789B1 (en) 2013-09-09 2020-07-08 vTv Therapeutics LLC Use of a ppar-delta agonists for treating muscle atrophy
KR101715127B1 (ko) * 2015-10-30 2017-03-15 한국과학기술연구원 시신경 척수염 예방 또는 치료용 피리미딘 카복실레이트 유도체
WO2021092279A1 (en) * 2019-11-06 2021-05-14 Board Of Regents, The University Of Texas System Methods for the treatment of dysmyelinating/demyelinating diseases
CN114195777B (zh) * 2020-09-18 2023-06-20 凯思凯迪（上海）医药科技有限公司 新型fxr小分子激动剂制备及其用途
CN114195786B (zh) * 2020-09-18 2023-08-22 凯思凯迪（上海）医药科技有限公司 新型fxr小分子激动剂制备及其用途
WO2023147309A1 (en) 2022-01-25 2023-08-03 Reneo Pharmaceuticals, Inc. Use of ppar-delta agonists in the treatment of disease

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RU2375358C2 (ru) * 2004-04-01 2009-12-10 Авентис Фармасьютикалз, Инк. 1,3,4-оксадиазол-2-оны в качестве модуляторов ppar-дельта и их применение
BRPI0508180A (pt) * 2004-04-01 2007-08-07 Aventis Pharma Inc 1,3,4-oxadiazol-2-onas como moduladores de ppar delta e seu uso deste

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Also Published As

Publication number Publication date
CN1956984B (zh) 2010-06-09
US7638539B2 (en) 2009-12-29
ZA200607852B (en) 2008-07-30
WO2005097763A3 (en) 2005-12-15
CN1956984A (zh) 2007-05-02
US20070099964A1 (en) 2007-05-03
CA2561230A1 (en) 2005-10-20
WO2005097763A2 (en) 2005-10-20
AU2005230838A1 (en) 2005-10-20
JP2007531764A (ja) 2007-11-08
BRPI0508180A (pt) 2007-08-07
US7872032B2 (en) 2011-01-18
IL178166A0 (en) 2006-12-31
US20090275621A1 (en) 2009-11-05
JP4813461B2 (ja) 2011-11-09
MA28563B1 (fr) 2007-04-03
SG151336A1 (en) 2009-04-30
RU2365589C2 (ru) 2009-08-27
RU2006138494A (ru) 2008-05-10
NO20064951L (no) 2006-10-30
NZ549823A (en) 2009-12-24

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